NO121340B - - Google Patents
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- Publication number
- NO121340B NO121340B NO165684A NO16568466A NO121340B NO 121340 B NO121340 B NO 121340B NO 165684 A NO165684 A NO 165684A NO 16568466 A NO16568466 A NO 16568466A NO 121340 B NO121340 B NO 121340B
- Authority
- NO
- Norway
- Prior art keywords
- dihydroxy
- tetrahydroisoquinoline
- trimethoxyphenyl
- hydrochloride
- formula
- Prior art date
Links
- 229940124630 bronchodilator Drugs 0.000 claims description 9
- 239000002253 acid Chemical group 0.000 claims description 7
- 230000003177 cardiotonic effect Effects 0.000 claims description 6
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 5
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 230000003182 bronchodilatating effect Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical class C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- -1 dimethoxy-mono-hydroxy-phenyl groups Chemical group 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- ZOLBALGTFCCTJF-UHFFFAOYSA-N 4-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol;sulfuric acid Chemical compound OS(O)(=O)=O.CC(C)NCC(O)C1=CC=C(O)C(O)=C1.CC(C)NCC(O)C1=CC=C(O)C(O)=C1 ZOLBALGTFCCTJF-UHFFFAOYSA-N 0.000 description 10
- 229940018435 isoproterenol sulfate Drugs 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CTENFNNZBMHDDG-UHFFFAOYSA-N Dopamine hydrochloride Chemical compound Cl.NCCC1=CC=C(O)C(O)=C1 CTENFNNZBMHDDG-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 230000000747 cardiac effect Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- UHSXRTHJCJGEKG-UHFFFAOYSA-N hydron;1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol;chloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CC2C3=CC(O)=C(O)C=C3CCN2)=C1 UHSXRTHJCJGEKG-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 150000003526 tetrahydroisoquinolines Chemical class 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 230000004531 blood pressure lowering effect Effects 0.000 description 2
- 239000000496 cardiotonic agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000000994 depressogenic effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- RGVPOXRFEPSFGH-UHFFFAOYSA-N 1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol Chemical compound COC1=C(OC)C(OC)=CC(CC2C3=CC(O)=C(O)C=C3CCN2)=C1 RGVPOXRFEPSFGH-UHFFFAOYSA-N 0.000 description 1
- GWCFOZUNGBECRW-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(O)=C(O)C=C2CCN1 GWCFOZUNGBECRW-UHFFFAOYSA-N 0.000 description 1
- ZVTWHNLKDVOCNW-UHFFFAOYSA-N 1-[(3,5-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol Chemical compound COC1=CC(OC)=CC(CC2C3=CC(O)=C(O)C=C3CCN2)=C1 ZVTWHNLKDVOCNW-UHFFFAOYSA-N 0.000 description 1
- FQDMSPFPWVUVKY-UHFFFAOYSA-N 2-(2,3,4-trimethoxyphenyl)acetaldehyde Chemical compound COC1=CC=C(CC=O)C(OC)=C1OC FQDMSPFPWVUVKY-UHFFFAOYSA-N 0.000 description 1
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- KJOJTPANXQIYQH-UHFFFAOYSA-N 2-phenyloxirane-2-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CO1 KJOJTPANXQIYQH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- LORRRHSFSDEKDU-UHFFFAOYSA-N N,N-dihydroxy-2-phenylethanamine hydrochloride Chemical compound Cl.ON(CCC1=CC=CC=C1)O LORRRHSFSDEKDU-UHFFFAOYSA-N 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000007675 cardiac surgery Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical class OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000003540 papillary muscle Anatomy 0.000 description 1
- 238000009519 pharmacological trial Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 210000005241 right ventricle Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7582065 | 1965-12-08 | ||
| JP3752466 | 1966-06-09 | ||
| JP4828366 | 1966-07-22 | ||
| JP4828266 | 1966-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121340B true NO121340B (fr) | 1971-02-15 |
Family
ID=27460434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO165684A NO121340B (fr) | 1965-12-08 | 1966-11-22 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3497516A (fr) |
| AT (1) | AT269882B (fr) |
| BE (1) | BE689865A (fr) |
| CH (1) | CH468384A (fr) |
| DE (1) | DE1620567A1 (fr) |
| DK (1) | DK123031B (fr) |
| ES (1) | ES343003A1 (fr) |
| FI (1) | FI48079C (fr) |
| FR (1) | FR5747M (fr) |
| GB (1) | GB1114660A (fr) |
| IL (1) | IL28215A (fr) |
| MY (1) | MY6900335A (fr) |
| NL (1) | NL6617017A (fr) |
| NO (1) | NO121340B (fr) |
| SE (1) | SE323963B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3818015A (en) * | 1970-12-17 | 1974-06-18 | Tanabe Seiyaku Co | 1(polymethoxybenzyl) 6 hydroxyl 1,2,3,4 tetrahydro isoquinolines |
| FR2119989B1 (fr) * | 1970-12-29 | 1975-10-10 | Fujisawa Pharmaceutical Co | |
| US3963725A (en) * | 1973-07-20 | 1976-06-15 | Fujisawa Pharmaceutical Co., Ltd. | 1,2,3,4-Tetrahydroisoquinoline derivatives and the preparation thereof |
| BG38182A1 (en) * | 1983-06-21 | 1985-11-15 | Ivanova | Tocolytic means |
| WO1999016752A1 (fr) * | 1997-09-30 | 1999-04-08 | Molecular Designs International, Inc. | AGONISTES DE β3-ADRENORECEPTEURS, COMPOSITIONS D'AGONISTES ET PROCEDES D'UTILISATION |
| US6593341B2 (en) | 2001-03-29 | 2003-07-15 | Molecular Design International, Inc. | β3-adrenoreceptor agonists, agonist compositions and methods of making and using the same |
| US6596734B1 (en) | 2002-10-11 | 2003-07-22 | Molecular Design International, Inc. | Tetrahydroisoquinoline compounds for use as β3-adrenoreceptor agonists |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL286505A (fr) * | 1961-12-15 |
-
1966
- 1966-09-15 US US579504A patent/US3497516A/en not_active Expired - Lifetime
- 1966-09-22 FR FR77345A patent/FR5747M/fr not_active Expired
- 1966-09-30 DE DE19661620567 patent/DE1620567A1/de active Pending
- 1966-11-17 BE BE689865D patent/BE689865A/xx not_active IP Right Cessation
- 1966-11-22 NO NO165684A patent/NO121340B/no unknown
- 1966-11-24 SE SE16115/66A patent/SE323963B/xx unknown
- 1966-12-02 NL NL6617017A patent/NL6617017A/xx unknown
- 1966-12-05 GB GB54413/66A patent/GB1114660A/en not_active Expired
- 1966-12-07 DK DK632566AA patent/DK123031B/da not_active IP Right Cessation
- 1966-12-08 CH CH1747666A patent/CH468384A/de unknown
-
1967
- 1967-06-28 IL IL28215A patent/IL28215A/xx unknown
- 1967-07-11 AT AT648267A patent/AT269882B/de active
- 1967-07-13 ES ES343003A patent/ES343003A1/es not_active Expired
- 1967-07-21 FI FI672013A patent/FI48079C/fi active
-
1969
- 1969-12-31 MY MY1969335A patent/MY6900335A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MY6900335A (en) | 1969-12-31 |
| NL6617017A (fr) | 1967-06-09 |
| DE1620567A1 (de) | 1970-04-30 |
| DK123031B (da) | 1972-05-08 |
| BE689865A (fr) | 1967-05-02 |
| FI48079B (fr) | 1974-02-28 |
| US3497516A (en) | 1970-02-24 |
| FI48079C (fi) | 1974-06-10 |
| ES343003A1 (es) | 1968-08-16 |
| SE323963B (fr) | 1970-05-19 |
| IL28215A (en) | 1971-02-25 |
| AT269882B (de) | 1969-04-10 |
| FR5747M (fr) | 1968-01-29 |
| GB1114660A (en) | 1968-05-22 |
| CH468384A (de) | 1969-02-15 |
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